A8054

D(−)-2-Amino-5-phosphonopentanoic acid

NMDA receptor antagonist

• Synonym(s): D(−)-AP-5, D(−)-APV, D-2-Amino-5-phosphonovaleric acid
• Empirical Formula (Hill Notation): C₅H₁₂NO₅P
• CAS Number: 79055-68-8
• Molecular Weight: 197.13
• MDL number: MFCD00078839
• UNSPSC Code: 12352106
• PubChem Substance ID: 24891311
• NACRES: NA.26

Properties

• Quality Level: 100
• Assay: ≥98% (TLC)
• form: powder
• optical purity: optical purity: ≥90% (HPLC, Marfey′s reagent)
• technique(s): ligand binding assay: suitable
• color: white
• mp: 245-246 °C
• SMILES string: N[C@H](CCCP(O)(O)=O)C(O)=O
• InChI: 1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m1/s1
• InChI key: VOROEQBFPPIACJ-SCSAIBSYSA-N
• Gene Information: mouse ... Grin2a(14811) ; rat ... Grik1(29559) , Grin2a(24409) , Grin2b(24410) , Grin2c(24411) , Grin2d(24412)

Description

Application

D(-)-2-Amino-5-phosphonopentanoic acid has been used to pretreat BNST (bed nucleus of the stria terminalis) in order to block the induction of anxiety by ORX-A (orexin-A) into the BNST.

Biochem/physiol Actions

NMDA antagonists have muscle relaxation property and are known to offer neuron protection against brain damage induced by ischemia. 2-Amino-5-phosphonopentanoic acid has been proved to block the iontophoresis induced depolarization of NMDA.

Anticonvulsant; potent and selective N-methyl-D-aspartate (NMDA) receptor antagonist; active enantiomer of 2-amino-5-phosphonopentanoic acid.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves